# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2026

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_dhxg1_0m
_database_code_depnum_ccdc_archive 'CCDC 2499665'
loop_
_audit_author_name
_audit_author_address
'hugen xie'
;Southwest University of Science and Technology
China
;
_audit_update_record             
;
2025-11-02 deposited with the CCDC.	2026-01-04 downloaded from the CCDC.
;
_audit_creation_date             2025-07-30
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H14 Cl N2, C6 F4 N9 O6'
_chemical_formula_sum            'C13 H14 Cl F4 N11 O6'
_chemical_formula_weight         531.80
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.0309(3)
_cell_length_b                   7.8291(2)
_cell_length_c                   23.1989(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.1040(10)
_cell_angle_gamma                90
_cell_volume                     2002.15(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9582
_cell_measurement_temperature    150.0(1)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.75
_shelx_estimated_absorpt_T_max   0.944
_shelx_estimated_absorpt_T_min   0.928
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_T_max  0.4908
_exptl_absorpt_correction_T_min  0.3553
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1226 before and 0.0705 after correction.
The Ratio of minimum to maximum transmission is 0.7239.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.764
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            22408
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.383
_diffrn_reflns_theta_min         2.075
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3408
_reflns_number_total             4078
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.41 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.41 (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4078
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0395
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0322P)²+1.5296P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.0990
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C7(H7A,H7B), C8(H8A,H8B), C12(H12A,H12B),
 C13(H13A,H13B), C9(H9A,H9B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.34261(5) 0.92821(7) 0.93897(2) 0.03665(15) Uani 1 1 d . . . . .
F4 F 0.60433(10) 0.37052(14) 0.49172(5) 0.0265(3) Uani 1 1 d . . . . .
F3 F 0.78032(11) 1.06577(18) 0.73664(6) 0.0444(4) Uani 1 1 d . . . . .
O3 O 0.76188(12) 0.20221(17) 0.60661(6) 0.0268(3) Uani 1 1 d . . . . .
F1 F 0.63920(15) 0.9976(2) 0.79300(6) 0.0529(4) Uani 1 1 d . . . . .
O4 O 0.78670(13) 0.19105(18) 0.51391(7) 0.0318(3) Uani 1 1 d . . . . .
F2 F 0.60368(14) 1.17148(17) 0.72405(7) 0.0525(4) Uani 1 1 d . . . . .
O5 O 0.52184(14) 0.07243(18) 0.58981(7) 0.0338(4) Uani 1 1 d . . . . .
O1 O 0.81843(15) 0.84747(18) 0.55330(7) 0.0360(4) Uani 1 1 d . . . . .
O6 O 0.43299(14) 0.1707(2) 0.51175(7) 0.0381(4) Uani 1 1 d . . . . .
N3 N 0.63726(13) 0.69435(18) 0.63873(6) 0.0160(3) Uani 1 1 d . . . . .
N5 N 0.47949(14) 0.43908(19) 0.61604(7) 0.0197(3) Uani 1 1 d . . . . .
N2 N 0.70422(13) 0.82629(19) 0.66198(7) 0.0183(3) Uani 1 1 d . . . . .
N11 N 0.38364(13) 0.66638(19) 0.86644(7) 0.0184(3) Uani 1 1 d . . . . .
N1 N 0.52111(14) 0.8033(2) 0.70516(7) 0.0206(3) Uani 1 1 d . . . . .
N6 N 0.77492(14) 0.57227(19) 0.57156(7) 0.0210(3) Uani 1 1 d . . . . .
N8 N 0.73075(14) 0.22606(19) 0.55654(7) 0.0208(3) Uani 1 1 d . . . . .
N7 N 0.85202(14) 0.71480(19) 0.57539(7) 0.0214(3) Uani 1 1 d . . . . .
O2 O 0.95276(14) 0.6891(2) 0.59655(9) 0.0449(4) Uani 1 1 d . . . . .
N4 N 0.44631(14) 0.5549(2) 0.65421(7) 0.0220(3) Uani 1 1 d . . . . .
N9 N 0.51135(14) 0.1709(2) 0.54971(7) 0.0240(4) Uani 1 1 d . . . . .
N10 N 0.28883(15) 0.4243(2) 0.80589(8) 0.0277(4) Uani 1 1 d . . . . .
C3 C 0.67387(16) 0.5789(2) 0.59815(7) 0.0161(4) Uani 1 1 d . . . . .
C2 C 0.58432(15) 0.4482(2) 0.59013(8) 0.0164(4) Uani 1 1 d . . . . .
C4 C 0.52795(15) 0.6800(2) 0.66578(8) 0.0178(4) Uani 1 1 d . . . . .
C5 C 0.62838(16) 0.8832(2) 0.70037(8) 0.0187(4) Uani 1 1 d . . . . .
C1 C 0.60654(16) 0.3139(2) 0.54655(8) 0.0188(4) Uani 1 1 d . . . . .
C10 C 0.48057(17) 0.5723(3) 0.83451(9) 0.0267(4) Uani 1 1 d . . . . .
H10A H 0.541793 0.524619 0.862329 0.032 Uiso 1 1 calc R . . . .
H10B H 0.522008 0.651904 0.808546 0.032 Uiso 1 1 calc R . . . .
C11 C 0.41991(19) 0.4272(3) 0.79916(9) 0.0291(5) Uani 1 1 d . . . . .
H11A H 0.437079 0.442558 0.757892 0.035 Uiso 1 1 calc R . . . .
H11B H 0.454864 0.316419 0.811887 0.035 Uiso 1 1 calc R . . . .
C7 C 0.44538(18) 0.8052(3) 0.90078(9) 0.0262(4) Uani 1 1 d . . . . .
H7A H 0.489667 0.880323 0.874447 0.031 Uiso 1 1 calc R . . . .
H7B H 0.505477 0.753553 0.928329 0.031 Uiso 1 1 calc R . . . .
C6 C 0.66335(18) 1.0304(2) 0.73862(9) 0.0249(4) Uani 1 1 d . . . . .
C8 C 0.29281(19) 0.7377(3) 0.82241(9) 0.0292(5) Uani 1 1 d . . . . .
H8A H 0.333253 0.819159 0.796738 0.035 Uiso 1 1 calc R . . . .
H8B H 0.227639 0.799052 0.842076 0.035 Uiso 1 1 calc R . . . .
C12 C 0.3231(2) 0.5395(3) 0.90484(9) 0.0305(5) Uani 1 1 d . . . . .
H12A H 0.260350 0.597383 0.927209 0.037 Uiso 1 1 calc R . . . .
H12B H 0.383723 0.488788 0.932329 0.037 Uiso 1 1 calc R . . . .
C13 C 0.2648(2) 0.3995(3) 0.86705(10) 0.0304(5) Uani 1 1 d . . . . .
H13A H 0.296958 0.286933 0.879697 0.036 Uiso 1 1 calc R . . . .
H13B H 0.176117 0.399218 0.872115 0.036 Uiso 1 1 calc R . . . .
C9 C 0.2388(2) 0.5884(3) 0.78694(11) 0.0362(5) Uani 1 1 d . . . . .
H9A H 0.149721 0.586916 0.790610 0.043 Uiso 1 1 calc R . . . .
H9B H 0.255770 0.605771 0.745742 0.043 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C7 1.753(2) . ?
F4 C1 1.347(2) . ?
F3 C6 1.322(2) . ?
O3 N8 1.214(2) . ?
F1 C6 1.324(2) . ?
O4 N8 1.216(2) . ?
F2 C6 1.324(2) . ?
O5 N9 1.210(2) . ?
O1 N7 1.210(2) . ?
O6 N9 1.211(2) . ?
N3 N2 1.369(2) . ?
N3 C3 1.377(2) . ?
N3 C4 1.384(2) . ?
N5 N4 1.328(2) . ?
N5 C2 1.325(2) . ?
N2 C5 1.321(2) . ?
N11 C10 1.514(2) . ?
N11 C7 1.496(2) . ?
N11 C8 1.511(2) . ?
N11 C12 1.507(2) . ?
N1 C4 1.333(2) . ?
N1 C5 1.347(2) . ?
N6 N7 1.404(2) . ?
N6 C3 1.295(2) . ?
N8 C1 1.543(2) . ?
N7 O2 1.215(2) . ?
N4 C4 1.351(2) . ?
N9 C1 1.538(2) . ?
N10 C11 1.460(3) . ?
N10 C13 1.466(3) . ?
N10 C9 1.459(3) . ?
C3 C2 1.429(2) . ?
C2 C1 1.486(3) . ?
C5 C6 1.496(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.540(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.537(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.530(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N3 C3 126.68(14) . . ?
N2 N3 C4 110.44(14) . . ?
C3 N3 C4 122.62(15) . . ?
C2 N5 N4 122.15(15) . . ?
C5 N2 N3 100.01(14) . . ?
C7 N11 C10 107.33(14) . . ?
C7 N11 C8 111.67(15) . . ?
C7 N11 C12 111.52(15) . . ?
C8 N11 C10 108.15(15) . . ?
C12 N11 C10 107.75(15) . . ?
C12 N11 C8 110.24(15) . . ?
C4 N1 C5 101.99(15) . . ?
C3 N6 N7 117.93(15) . . ?
O3 N8 O4 127.55(16) . . ?
O3 N8 C1 115.52(15) . . ?
O4 N8 C1 116.92(16) . . ?
O1 N7 N6 118.68(16) . . ?
O1 N7 O2 125.07(17) . . ?
O2 N7 N6 115.90(15) . . ?
N5 N4 C4 115.43(15) . . ?
O5 N9 O6 127.15(17) . . ?
O5 N9 C1 116.98(15) . . ?
O6 N9 C1 115.87(16) . . ?
C11 N10 C13 108.68(16) . . ?
C9 N10 C11 108.58(17) . . ?
C9 N10 C13 109.19(18) . . ?
N3 C3 C2 109.89(15) . . ?
N6 C3 N3 129.15(16) . . ?
N6 C3 C2 120.83(16) . . ?
N5 C2 C3 126.19(16) . . ?
N5 C2 C1 116.04(15) . . ?
C3 C2 C1 117.69(16) . . ?
N1 C4 N3 108.91(15) . . ?
N1 C4 N4 127.38(17) . . ?
N4 C4 N3 123.67(16) . . ?
N2 C5 N1 118.62(16) . . ?
N2 C5 C6 120.22(16) . . ?
N1 C5 C6 121.13(16) . . ?
F4 C1 N8 105.89(14) . . ?
F4 C1 N9 107.21(14) . . ?
F4 C1 C2 114.32(15) . . ?
N9 C1 N8 105.82(13) . . ?
C2 C1 N8 112.41(14) . . ?
C2 C1 N9 110.67(15) . . ?
N11 C10 H10A 110.0 . . ?
N11 C10 H10B 110.0 . . ?
N11 C10 C11 108.57(15) . . ?
H10A C10 H10B 108.4 . . ?
C11 C10 H10A 110.0 . . ?
C11 C10 H10B 110.0 . . ?
N10 C11 C10 111.55(16) . . ?
N10 C11 H11A 109.3 . . ?
N10 C11 H11B 109.3 . . ?
C10 C11 H11A 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
Cl1 C7 H7A 109.2 . . ?
Cl1 C7 H7B 109.2 . . ?
N11 C7 Cl1 112.21(13) . . ?
N11 C7 H7A 109.2 . . ?
N11 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
F3 C6 F1 107.74(17) . . ?
F3 C6 F2 107.03(17) . . ?
F3 C6 C5 111.81(16) . . ?
F1 C6 C5 111.05(16) . . ?
F2 C6 F1 106.83(17) . . ?
F2 C6 C5 112.11(16) . . ?
N11 C8 H8A 110.0 . . ?
N11 C8 H8B 110.0 . . ?
N11 C8 C9 108.37(16) . . ?
H8A C8 H8B 108.4 . . ?
C9 C8 H8A 110.0 . . ?
C9 C8 H8B 110.0 . . ?
N11 C12 H12A 110.0 . . ?
N11 C12 H12B 110.0 . . ?
N11 C12 C13 108.63(16) . . ?
H12A C12 H12B 108.3 . . ?
C13 C12 H12A 110.0 . . ?
C13 C12 H12B 110.0 . . ?
N10 C13 C12 111.88(16) . . ?
N10 C13 H13A 109.2 . . ?
N10 C13 H13B 109.2 . . ?
C12 C13 H13A 109.2 . . ?
C12 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
N10 C9 C8 111.94(16) . . ?
N10 C9 H9A 109.2 . . ?
N10 C9 H9B 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 N8 C1 F4 163.36(14) . . . . ?
O3 N8 C1 N9 -83.04(17) . . . . ?
O3 N8 C1 C2 37.9(2) . . . . ?
O4 N8 C1 F4 -15.6(2) . . . . ?
O4 N8 C1 N9 97.97(17) . . . . ?
O4 N8 C1 C2 -141.12(16) . . . . ?
O5 N9 C1 F4 159.93(16) . . . . ?
O5 N9 C1 N8 47.2(2) . . . . ?
O5 N9 C1 C2 -74.8(2) . . . . ?
O6 N9 C1 F4 -20.8(2) . . . . ?
O6 N9 C1 N8 -133.51(16) . . . . ?
O6 N9 C1 C2 104.46(18) . . . . ?
N3 N2 C5 N1 0.6(2) . . . . ?
N3 N2 C5 C6 178.93(16) . . . . ?
N3 C3 C2 N5 1.8(2) . . . . ?
N3 C3 C2 C1 178.39(15) . . . . ?
N5 N4 C4 N3 2.6(2) . . . . ?
N5 N4 C4 N1 -174.59(17) . . . . ?
N5 C2 C1 F4 109.99(18) . . . . ?
N5 C2 C1 N8 -129.26(16) . . . . ?
N5 C2 C1 N9 -11.2(2) . . . . ?
N2 N3 C3 N6 -3.1(3) . . . . ?
N2 N3 C3 C2 172.85(15) . . . . ?
N2 N3 C4 N1 1.70(19) . . . . ?
N2 N3 C4 N4 -175.97(16) . . . . ?
N2 C5 C6 F3 -12.7(3) . . . . ?
N2 C5 C6 F1 -133.07(19) . . . . ?
N2 C5 C6 F2 107.5(2) . . . . ?
N11 C10 C11 N10 0.9(2) . . . . ?
N11 C8 C9 N10 0.5(3) . . . . ?
N11 C12 C13 N10 2.5(2) . . . . ?
N1 C5 C6 F3 165.61(17) . . . . ?
N1 C5 C6 F1 45.2(2) . . . . ?
N1 C5 C6 F2 -74.2(2) . . . . ?
N6 C3 C2 N5 178.12(17) . . . . ?
N6 C3 C2 C1 -5.3(2) . . . . ?
N7 N6 C3 N3 -12.5(3) . . . . ?
N7 N6 C3 C2 171.92(16) . . . . ?
N4 N5 C2 C3 -0.7(3) . . . . ?
N4 N5 C2 C1 -177.36(15) . . . . ?
C3 N3 N2 C5 -175.50(16) . . . . ?
C3 N3 C4 N1 176.16(15) . . . . ?
C3 N3 C4 N4 -1.5(3) . . . . ?
C3 N6 N7 O1 -66.2(2) . . . . ?
C3 N6 N7 O2 120.2(2) . . . . ?
C3 C2 C1 F4 -67.0(2) . . . . ?
C3 C2 C1 N8 53.8(2) . . . . ?
C3 C2 C1 N9 171.86(14) . . . . ?
C2 N5 N4 C4 -1.5(2) . . . . ?
C4 N3 N2 C5 -1.33(18) . . . . ?
C4 N3 C3 N6 -176.61(17) . . . . ?
C4 N3 C3 C2 -0.7(2) . . . . ?
C4 N1 C5 N2 0.4(2) . . . . ?
C4 N1 C5 C6 -177.94(17) . . . . ?
C5 N1 C4 N3 -1.21(18) . . . . ?
C5 N1 C4 N4 176.35(18) . . . . ?
C10 N11 C7 Cl1 178.69(13) . . . . ?
C10 N11 C8 C9 59.1(2) . . . . ?
C10 N11 C12 C13 -61.0(2) . . . . ?
C11 N10 C13 C12 58.0(2) . . . . ?
C11 N10 C9 C8 -60.0(2) . . . . ?
C7 N11 C10 C11 179.44(16) . . . . ?
C7 N11 C8 C9 176.95(17) . . . . ?
C7 N11 C12 C13 -178.59(16) . . . . ?
C8 N11 C10 C11 -59.9(2) . . . . ?
C8 N11 C7 Cl1 60.32(19) . . . . ?
C8 N11 C12 C13 56.8(2) . . . . ?
C12 N11 C10 C11 59.2(2) . . . . ?
C12 N11 C7 Cl1 -63.51(19) . . . . ?
C12 N11 C8 C9 -58.5(2) . . . . ?
C13 N10 C11 C10 -59.7(2) . . . . ?
C13 N10 C9 C8 58.3(2) . . . . ?
C9 N10 C11 C10 59.0(2) . . . . ?
C9 N10 C13 C12 -60.3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_y1_0m
_database_code_depnum_ccdc_archive 'CCDC 2499666'
loop_
_audit_author_name
_audit_author_address
'hugen xie'
;Southwest University of Science and Technology
China
;
_audit_update_record             
;
2025-11-02 deposited with the CCDC.	2026-01-04 downloaded from the CCDC.
;
_audit_creation_date             2025-07-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C6 H3 F3 N10 O), H2 O, C3 H7 N O'
_chemical_formula_sum            'C15 H15 F6 N21 O4'
_chemical_formula_weight         667.48
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1445(6)
_cell_length_b                   10.7710(7)
_cell_length_c                   15.6123(12)
_cell_angle_alpha                86.096(2)
_cell_angle_beta                 79.109(3)
_cell_angle_gamma                86.365(2)
_cell_volume                     1340.00(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2751
_cell_measurement_temperature    170.0(1)
_cell_measurement_theta_max      25.46
_cell_measurement_theta_min      2.66
_shelx_estimated_absorpt_T_max   0.970
_shelx_estimated_absorpt_T_min   0.964
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5269
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1218 before and 0.0780 after correction.
The Ratio of minimum to maximum transmission is 0.7069.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.654
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0931
_diffrn_reflns_av_unetI/netI     0.1165
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14988
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.392
_diffrn_reflns_theta_min         1.898
_diffrn_ambient_temperature      170.0(1)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3038
_reflns_number_total             5461
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.41 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.41 (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     464
_refine_ls_number_reflns         5461
_refine_ls_number_restraints     396
_refine_ls_R_factor_all          0.1608
_refine_ls_R_factor_gt           0.0788
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0325P)²+3.2749P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1530
_refine_ls_wR_factor_ref         0.1917
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 F2-C1 \\sim F2A-C1
 with sigma of 0.02
 F5-C9 \\sim F5A-C9
 with sigma of 0.02
 F1-C1 \\sim F1A-C1
 with sigma of 0.02
 F3-C1 \\sim F3A-C1
 with sigma of 0.02
 F4-C9 \\sim F4A-C9
 with sigma of 0.02
 F6-C9 \\sim F6A-C9
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F5) = Uanis(F5A)
Uanis(F6) = Uanis(F6A)
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: F2(0.5) F1(0.5) F3(0.5) F4(0.5) F6(0.5) F5(0.5) F6A(0.5) F4A(0.5)
 F5A(0.5) F3A(0.5) F2A(0.5) F1A(0.5)
6.a Free rotating group:
 O3(H3A,H3B)
6.b Aromatic/amide H refined with riding coordinates:
 C16(H16)
6.c X=CH2 refined with riding coordinates:
 N10(H10A,H10B), N18(H18A,H18B)
6.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C6(H6A,H6B,H6C)
6.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 1.0019(4) 0.7544(3) 0.64086(19) 0.0283(8) Uani 1 1 d . . . . .
H2 H 1.068274 0.810749 0.621849 0.042 Uiso 1 1 calc R U . . .
F2 F 0.534(2) 0.441(3) 0.175(3) 0.050(6) Uani 0.5 1 d D . P A 1
O3 O 0.5797(4) 0.3202(3) 0.7170(2) 0.0333(8) Uani 1 1 d G . . . .
H3A H 0.612705 0.370914 0.672069 0.050 Uiso 1 1 d G U . . .
H3B H 0.666592 0.307448 0.742002 0.050 Uiso 1 1 d G U . . .
O4 O 0.3837(4) 0.1433(3) 0.7110(2) 0.0341(8) Uani 1 1 d . . . . .
H4 H 0.441247 0.203755 0.715312 0.051 Uiso 1 1 calc R U . . .
O1 O 1.1072(4) 0.6951(3) 0.2276(2) 0.0352(8) Uani 1 1 d . . . . .
N2 N 0.7758(4) 0.5226(3) 0.3826(2) 0.0193(8) Uani 1 1 d . . . . .
F1 F 0.788(4) 0.499(3) 0.128(2) 0.050(4) Uani 0.5 1 d D . P A 1
N5 N 0.6950(4) 0.4575(3) 0.5522(2) 0.0220(8) Uani 1 1 d . . . . .
F3 F 0.783(4) 0.3222(17) 0.160(3) 0.058(5) Uani 0.5 1 d D . P A 1
N10 N 0.9485(4) 0.6771(3) 0.3995(2) 0.0232(8) Uani 1 1 d . . . . .
H10A H 0.970864 0.688700 0.342253 0.028 Uiso 1 1 calc R U . . .
H10B H 0.995107 0.722681 0.432075 0.028 Uiso 1 1 calc R U . . .
N9 N 0.9515(4) 0.7032(3) 0.5710(2) 0.0244(9) Uani 1 1 d . . . . .
N14 N 0.3759(5) 0.1320(3) 0.6240(2) 0.0273(9) Uani 1 1 d . . . . .
N18 N 0.4427(4) 0.1896(3) 0.4508(2) 0.0242(9) Uani 1 1 d . . . . .
H18A H 0.485979 0.228594 0.401032 0.029 Uiso 1 1 calc R U . . .
H18B H 0.464249 0.212976 0.500237 0.029 Uiso 1 1 calc R U . . .
N13 N 0.3142(4) 0.0621(3) 0.3735(2) 0.0239(8) Uani 1 1 d . . . . .
N3 N 0.6268(5) 0.3776(3) 0.3455(2) 0.0259(9) Uani 1 1 d . . . . .
N4 N 0.6331(5) 0.3912(3) 0.4981(2) 0.0257(9) Uani 1 1 d . . . . .
F4 F 0.456(3) 0.1516(18) 0.121(3) 0.063(5) Uani 0.5 1 d D . P B 1
N1 N 0.7972(5) 0.5379(3) 0.2940(2) 0.0249(8) Uani 1 1 d . . . . .
N20 N 0.1746(4) -0.0741(3) 0.5141(2) 0.0263(9) Uani 1 1 d . . . . .
N19 N 0.1460(5) -0.1053(3) 0.4372(2) 0.0280(9) Uani 1 1 d . . . . .
N7 N 0.8314(5) 0.6007(4) 0.7445(3) 0.0299(9) Uani 1 1 d . . . . .
N11 N 0.2142(5) -0.0463(3) 0.2828(3) 0.0318(9) Uani 1 1 d . . . . .
N6 N 0.7914(5) 0.5616(4) 0.6779(2) 0.0347(10) Uani 1 1 d . . . . .
N12 N 0.3773(5) 0.1159(3) 0.2933(2) 0.0294(9) Uani 1 1 d . . . . .
N16 N 0.1876(5) -0.0276(4) 0.7547(3) 0.0397(11) Uani 1 1 d . . . . .
N15 N 0.1956(5) -0.0393(4) 0.6747(3) 0.0390(11) Uani 1 1 d . . . . .
F6 F 0.467(4) -0.023(3) 0.114(4) 0.080(6) Uani 0.5 1 d D . P B 1
F5 F 0.222(4) 0.053(3) 0.108(3) 0.076(6) Uani 0.5 1 d D . P B 1
C4 C 0.8454(5) 0.5914(4) 0.4365(3) 0.0193(9) Uani 1 1 d . . . . .
C3 C 0.6744(5) 0.4260(4) 0.4131(3) 0.0217(9) Uani 1 1 d . . . . .
C8 C 0.8538(5) 0.6127(4) 0.5949(3) 0.0210(9) Uani 1 1 d . . . . .
C5 C 0.7946(5) 0.5528(4) 0.5254(3) 0.0193(9) Uani 1 1 d . . . . .
C14 C 0.3453(5) 0.0961(4) 0.4511(3) 0.0226(9) Uani 1 1 d . . . . .
C12 C 0.2668(5) 0.0216(4) 0.5236(3) 0.0236(10) Uani 1 1 d . . . . .
N00Z N 1.0843(6) 0.7367(5) 0.0862(3) 0.0483(12) Uani 1 1 d . . . . .
C2 C 0.7049(6) 0.4491(4) 0.2776(3) 0.0261(10) Uani 1 1 d . . . . .
N8 N 0.8502(6) 0.6178(4) 0.8122(3) 0.0448(12) Uani 1 1 d . . . . .
C13 C 0.2829(5) 0.0441(4) 0.6133(3) 0.0254(10) Uani 1 1 d . . . . .
C11 C 0.2169(5) -0.0355(4) 0.3670(3) 0.0255(10) Uani 1 1 d . . . . .
C10 C 0.3117(6) 0.0456(4) 0.2436(3) 0.0305(11) Uani 1 1 d . . . . .
N17 N 0.1612(7) -0.0338(5) 0.8284(3) 0.0607(15) Uani 1 1 d . . . . .
C16 C 1.0244(7) 0.7287(4) 0.1702(3) 0.0365(12) Uani 1 1 d . . . . .
H16 H 0.908802 0.750161 0.188677 0.044 Uiso 1 1 calc R U . . .
C1 C 0.6925(7) 0.4252(5) 0.1864(3) 0.0363(11) Uani 1 1 d D . . . .
C9 C 0.3512(7) 0.0627(5) 0.1466(3) 0.0441(12) Uani 1 1 d D . . . .
C15 C 1.2586(8) 0.7033(8) 0.0527(4) 0.082(2) Uani 1 1 d . . . . .
H15A H 1.320812 0.695415 0.100876 0.123 Uiso 1 1 calc R U . . .
H15B H 1.305742 0.768204 0.009626 0.123 Uiso 1 1 calc R U . . .
H15C H 1.267027 0.623728 0.024850 0.123 Uiso 1 1 calc R U . . .
C6 C 0.9768(9) 0.7747(8) 0.0242(4) 0.088(3) Uani 1 1 d . . . . .
H6A H 0.981059 0.709243 -0.016981 0.132 Uiso 1 1 calc R U . . .
H6B H 1.014955 0.852074 -0.007939 0.132 Uiso 1 1 calc R U . . .
H6C H 0.861484 0.788325 0.055403 0.132 Uiso 1 1 calc R U . . .
F6A F 0.425(4) -0.038(3) 0.109(4) 0.080(6) Uani 0.5 1 d D . P B 2
F4A F 0.412(3) 0.1729(16) 0.119(3) 0.058(5) Uani 0.5 1 d D . P B 2
F5A F 0.213(4) 0.091(3) 0.115(3) 0.076(6) Uani 0.5 1 d D . P B 2
F3A F 0.743(4) 0.3077(15) 0.168(3) 0.050(5) Uani 0.5 1 d D . P A 2
F2A F 0.538(2) 0.410(3) 0.174(3) 0.047(5) Uani 0.5 1 d D . P A 2
F1A F 0.747(4) 0.520(3) 0.130(2) 0.060(7) Uani 0.5 1 d D . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 H2 0.8400 . ?
O2 N9 1.394(4) . ?
F2 C1 1.332(12) . ?
O3 H3A 0.8700 . ?
O3 H3B 0.8700 . ?
O4 H4 0.8400 . ?
O4 N14 1.386(5) . ?
O1 C16 1.241(6) . ?
N2 N1 1.361(5) . ?
N2 C4 1.377(5) . ?
N2 C3 1.373(5) . ?
F1 C1 1.335(12) . ?
N5 N4 1.329(5) . ?
N5 C5 1.343(5) . ?
F3 C1 1.336(13) . ?
N10 H10A 0.8800 . ?
N10 H10B 0.8800 . ?
N10 C4 1.316(5) . ?
N9 C8 1.288(5) . ?
N14 C13 1.288(5) . ?
N18 H18A 0.8800 . ?
N18 H18B 0.8800 . ?
N18 C14 1.320(5) . ?
N13 N12 1.364(5) . ?
N13 C14 1.363(5) . ?
N13 C11 1.376(5) . ?
N3 C3 1.338(5) . ?
N3 C2 1.348(5) . ?
N4 C3 1.339(5) . ?
F4 C9 1.317(12) . ?
N1 C2 1.319(5) . ?
N20 N19 1.333(5) . ?
N20 C12 1.346(5) . ?
N19 C11 1.344(6) . ?
N7 N6 1.253(5) . ?
N7 N8 1.125(5) . ?
N11 C11 1.331(6) . ?
N11 C10 1.348(6) . ?
N6 C8 1.389(5) . ?
N12 C10 1.323(6) . ?
N16 N15 1.254(6) . ?
N16 N17 1.127(6) . ?
N15 C13 1.391(6) . ?
F6 C9 1.333(13) . ?
F5 C9 1.320(13) . ?
C4 C5 1.414(6) . ?
C8 C5 1.469(6) . ?
C14 C12 1.414(6) . ?
C12 C13 1.468(6) . ?
N00Z C16 1.309(6) . ?
N00Z C15 1.448(8) . ?
N00Z C6 1.447(7) . ?
C2 C1 1.487(6) . ?
C10 C9 1.490(7) . ?
C16 H16 0.9500 . ?
C1 F3A 1.340(12) . ?
C1 F2A 1.337(13) . ?
C1 F1A 1.339(12) . ?
C9 F6A 1.324(13) . ?
C9 F4A 1.329(12) . ?
C9 F5A 1.324(13) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N9 O2 H2 109.5 . . ?
H3A O3 H3B 104.5 . . ?
N14 O4 H4 109.5 . . ?
N1 N2 C4 126.3(3) . . ?
N1 N2 C3 110.7(3) . . ?
C3 N2 C4 123.0(3) . . ?
N4 N5 C5 123.6(4) . . ?
H10A N10 H10B 120.0 . . ?
C4 N10 H10A 120.0 . . ?
C4 N10 H10B 120.0 . . ?
C8 N9 O2 113.1(3) . . ?
C13 N14 O4 112.6(4) . . ?
H18A N18 H18B 120.0 . . ?
C14 N18 H18A 120.0 . . ?
C14 N18 H18B 120.0 . . ?
N12 N13 C11 111.6(3) . . ?
C14 N13 N12 125.4(3) . . ?
C14 N13 C11 123.0(4) . . ?
C3 N3 C2 101.6(3) . . ?
N5 N4 C3 115.7(3) . . ?
C2 N1 N2 100.3(3) . . ?
N19 N20 C12 123.7(4) . . ?
N20 N19 C11 116.1(4) . . ?
N8 N7 N6 166.9(5) . . ?
C11 N11 C10 102.4(4) . . ?
N7 N6 C8 121.3(4) . . ?
C10 N12 N13 99.5(3) . . ?
N17 N16 N15 167.7(5) . . ?
N16 N15 C13 120.4(4) . . ?
N2 C4 C5 111.7(3) . . ?
N10 C4 N2 117.7(4) . . ?
N10 C4 C5 130.6(4) . . ?
N3 C3 N2 109.1(4) . . ?
N3 C3 N4 128.0(4) . . ?
N4 C3 N2 122.9(4) . . ?
N9 C8 N6 130.1(4) . . ?
N9 C8 C5 116.9(4) . . ?
N6 C8 C5 113.0(3) . . ?
N5 C5 C4 123.1(4) . . ?
N5 C5 C8 115.6(4) . . ?
C4 C5 C8 121.3(3) . . ?
N18 C14 N13 118.6(4) . . ?
N18 C14 C12 128.2(4) . . ?
N13 C14 C12 113.1(4) . . ?
N20 C12 C14 121.9(4) . . ?
N20 C12 C13 116.4(4) . . ?
C14 C12 C13 121.7(4) . . ?
C16 N00Z C15 120.9(5) . . ?
C16 N00Z C6 120.9(5) . . ?
C6 N00Z C15 118.2(5) . . ?
N3 C2 C1 120.7(4) . . ?
N1 C2 N3 118.4(4) . . ?
N1 C2 C1 120.9(4) . . ?
N14 C13 N15 129.8(4) . . ?
N14 C13 C12 117.7(4) . . ?
N15 C13 C12 112.4(4) . . ?
N19 C11 N13 122.2(4) . . ?
N11 C11 N13 108.2(4) . . ?
N11 C11 N19 129.6(4) . . ?
N11 C10 C9 120.5(4) . . ?
N12 C10 N11 118.3(4) . . ?
N12 C10 C9 121.1(4) . . ?
O1 C16 N00Z 125.0(5) . . ?
O1 C16 H16 117.5 . . ?
N00Z C16 H16 117.5 . . ?
F2 C1 F1 109(2) . . ?
F2 C1 F3 119(3) . . ?
F2 C1 C2 111(2) . . ?
F1 C1 F3 93(2) . . ?
F1 C1 C2 112.2(17) . . ?
F3 C1 C2 111(2) . . ?
F3A C1 C2 111(2) . . ?
F2A C1 C2 115(2) . . ?
F2A C1 F3A 93(2) . . ?
F2A C1 F1A 104(2) . . ?
F1A C1 C2 112.2(18) . . ?
F1A C1 F3A 120(3) . . ?
F4 C9 F6 91(3) . . ?
F4 C9 F5 120(3) . . ?
F4 C9 C10 111.6(18) . . ?
F6 C9 C10 110(3) . . ?
F5 C9 F6 106(2) . . ?
F5 C9 C10 115(2) . . ?
F6A C9 C10 112(3) . . ?
F6A C9 F4A 119(3) . . ?
F6A C9 F5A 108(2) . . ?
F4A C9 C10 112.7(19) . . ?
F5A C9 C10 110(2) . . ?
F5A C9 F4A 92(2) . . ?
N00Z C15 H15A 109.5 . . ?
N00Z C15 H15B 109.5 . . ?
N00Z C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N00Z C6 H6A 109.5 . . ?
N00Z C6 H6B 109.5 . . ?
N00Z C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 N9 C8 N6 1.0(7) . . . . ?
O2 N9 C8 C5 -179.9(3) . . . . ?
O4 N14 C13 N15 -1.4(7) . . . . ?
O4 N14 C13 C12 -179.1(4) . . . . ?
N2 N1 C2 N3 -0.3(5) . . . . ?
N2 N1 C2 C1 -178.0(4) . . . . ?
N2 C4 C5 N5 2.1(6) . . . . ?
N2 C4 C5 C8 179.8(4) . . . . ?
N5 N4 C3 N2 0.9(6) . . . . ?
N5 N4 C3 N3 -178.4(4) . . . . ?
N10 C4 C5 N5 -175.7(4) . . . . ?
N10 C4 C5 C8 2.0(7) . . . . ?
N9 C8 C5 N5 179.0(4) . . . . ?
N9 C8 C5 C4 1.1(6) . . . . ?
N18 C14 C12 N20 -177.7(4) . . . . ?
N18 C14 C12 C13 1.7(7) . . . . ?
N13 N12 C10 N11 0.1(5) . . . . ?
N13 N12 C10 C9 -176.8(4) . . . . ?
N13 C14 C12 N20 1.3(6) . . . . ?
N13 C14 C12 C13 -179.2(4) . . . . ?
N3 C2 C1 F2 62.6(18) . . . . ?
N3 C2 C1 F1 -175.4(16) . . . . ?
N3 C2 C1 F3 -72.7(15) . . . . ?
N3 C2 C1 F3A -55.9(14) . . . . ?
N3 C2 C1 F2A 47.7(18) . . . . ?
N3 C2 C1 F1A 166.7(16) . . . . ?
N4 N5 C5 C4 -0.7(6) . . . . ?
N4 N5 C5 C8 -178.5(4) . . . . ?
N1 N2 C4 N10 -3.2(6) . . . . ?
N1 N2 C4 C5 178.7(4) . . . . ?
N1 N2 C3 N3 -0.5(5) . . . . ?
N1 N2 C3 N4 180.0(4) . . . . ?
N1 C2 C1 F2 -119.7(18) . . . . ?
N1 C2 C1 F1 2.3(17) . . . . ?
N1 C2 C1 F3 105.0(15) . . . . ?
N1 C2 C1 F3A 121.8(14) . . . . ?
N1 C2 C1 F2A -134.6(18) . . . . ?
N1 C2 C1 F1A -15.6(16) . . . . ?
N20 N19 C11 N13 0.3(6) . . . . ?
N20 N19 C11 N11 178.0(4) . . . . ?
N20 C12 C13 N14 177.3(4) . . . . ?
N20 C12 C13 N15 -0.7(6) . . . . ?
N19 N20 C12 C14 -1.6(6) . . . . ?
N19 N20 C12 C13 178.9(4) . . . . ?
N7 N6 C8 N9 -1.8(8) . . . . ?
N7 N6 C8 C5 179.0(4) . . . . ?
N11 C10 C9 F4 -176.0(13) . . . . ?
N11 C10 C9 F6 -76.4(19) . . . . ?
N11 C10 C9 F5 43.2(17) . . . . ?
N11 C10 C9 F6A -57.9(19) . . . . ?
N11 C10 C9 F4A 164.4(13) . . . . ?
N11 C10 C9 F5A 63.1(17) . . . . ?
N6 C8 C5 N5 -1.7(5) . . . . ?
N6 C8 C5 C4 -179.6(4) . . . . ?
N12 N13 C14 N18 0.9(6) . . . . ?
N12 N13 C14 C12 -178.3(4) . . . . ?
N12 N13 C11 N19 177.7(4) . . . . ?
N12 N13 C11 N11 -0.4(5) . . . . ?
N12 C10 C9 F4 0.9(14) . . . . ?
N12 C10 C9 F6 100.5(19) . . . . ?
N12 C10 C9 F5 -140.0(17) . . . . ?
N12 C10 C9 F6A 118.9(19) . . . . ?
N12 C10 C9 F4A -18.7(14) . . . . ?
N12 C10 C9 F5A -120.1(17) . . . . ?
N16 N15 C13 N14 6.9(8) . . . . ?
N16 N15 C13 C12 -175.3(4) . . . . ?
C4 N2 N1 C2 179.8(4) . . . . ?
C4 N2 C3 N3 -179.9(4) . . . . ?
C4 N2 C3 N4 0.6(6) . . . . ?
C3 N2 N1 C2 0.5(4) . . . . ?
C3 N2 C4 N10 176.1(4) . . . . ?
C3 N2 C4 C5 -2.0(6) . . . . ?
C3 N3 C2 N1 0.0(6) . . . . ?
C3 N3 C2 C1 177.7(4) . . . . ?
C5 N5 N4 C3 -0.9(6) . . . . ?
C14 N13 N12 C10 178.3(4) . . . . ?
C14 N13 C11 N19 -0.5(7) . . . . ?
C14 N13 C11 N11 -178.6(4) . . . . ?
C14 C12 C13 N14 -2.2(6) . . . . ?
C14 C12 C13 N15 179.8(4) . . . . ?
C12 N20 N19 C11 0.7(6) . . . . ?
C2 N3 C3 N2 0.3(5) . . . . ?
C2 N3 C3 N4 179.8(4) . . . . ?
N8 N7 N6 C8 -175(2) . . . . ?
C11 N13 N12 C10 0.2(5) . . . . ?
C11 N13 C14 N18 178.8(4) . . . . ?
C11 N13 C14 C12 -0.4(6) . . . . ?
C11 N11 C10 N12 -0.4(6) . . . . ?
C11 N11 C10 C9 176.5(4) . . . . ?
C10 N11 C11 N13 0.4(5) . . . . ?
C10 N11 C11 N19 -177.5(5) . . . . ?
N17 N16 N15 C13 173(3) . . . . ?
C15 N00Z C16 O1 1.2(9) . . . . ?
C6 N00Z C16 O1 178.8(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2499667'
loop_
_audit_author_name
_audit_author_address
'hugen xie'
;Southwest University of Science and Technology
China
;
_audit_update_record             
;
2025-11-02 deposited with the CCDC.	2026-01-04 downloaded from the CCDC.
;
_audit_creation_date             2025-06-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H2 F3 N8 O4, H2 O, H4 N'
_chemical_formula_sum            'C6 H8 F3 N9 O5'
_chemical_formula_weight         343.21
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.0942(14)
_cell_length_b                   13.4468(18)
_cell_length_c                   10.1321(15)
_cell_angle_alpha                90
_cell_angle_beta                 92.162(6)
_cell_angle_gamma                90
_cell_volume                     1238.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2345
_cell_measurement_temperature    150.0(1)
_cell_measurement_theta_max      26.22
_cell_measurement_theta_min      2.24
_shelx_estimated_absorpt_T_max   0.964
_shelx_estimated_absorpt_T_min   0.957
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5238
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1561 before and 0.0978 after correction.
The Ratio of minimum to maximum transmission is 0.7027.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.841
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0956
_diffrn_reflns_av_unetI/netI     0.0936
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8515
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.398
_diffrn_reflns_theta_min         2.241
_diffrn_ambient_temperature      150.0(1)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1685
_reflns_number_total             2506
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.41 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.41 (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.730
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.106
_refine_ls_extinction_coef       0.018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         2506
_refine_ls_number_restraints     205
_refine_ls_R_factor_all          0.1223
_refine_ls_R_factor_gt           0.0768
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0614P)²+3.2482P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1652
_refine_ls_wR_factor_ref         0.1919
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All O(H,H) groups, {H9A,H9B} of N9
 At 1.2 times of:
  {H4A,H4B} of N4
2. Restrained distances
 F3-C1 \\sim F3A-C1
 with sigma of 0.02
 F1-C1 \\sim F1A-C1
 with sigma of 0.02
 F2-C1 \\sim F2A-C1
 with sigma of 0.02
 H9A-H9D \\sim H9D-H9C
 with sigma of 0.02
 H9B-H9C \\sim H9C-H9A
 with sigma of 0.02
 H9D-H9B \\sim H9B-H9C
 with sigma of 0.02
 H9D-H9B \\sim H9B-H9A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F3) = Uanis(F3A)
Uanis(F1) = Uanis(F1A)
Uanis(F2) = Uanis(F2A)
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: F3(0.5) F2(0.5) F1(0.5) F1A(0.5) F3A(0.5) F2A(0.5)
6.a Free rotating group:
 O5(H5A,H5B), N9(H9A,H9B)
6.b X=CH2 refined with riding coordinates:
 N4(H4A,H4B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F3 F 0.6148(15) 0.3796(19) 0.643(3) 0.0278(16) Uani 0.5 1 d D . P A 1
O2 O 0.4356(3) 1.0131(2) 0.3326(3) 0.0234(7) Uani 1 1 d . . . . .
O1 O 0.4298(3) 0.8523(2) 0.3032(3) 0.0236(7) Uani 1 1 d . . . . .
F2 F 0.7154(17) 0.3401(12) 0.4658(14) 0.0333(18) Uani 0.5 1 d D . P A 1
O3 O 0.6891(3) 1.0843(2) 0.4246(3) 0.0251(7) Uani 1 1 d . . . . .
F1 F 0.8350(12) 0.3983(11) 0.6695(10) 0.0327(16) Uani 0.5 1 d D . P A 1
O4 O 0.8578(3) 0.9727(2) 0.4667(3) 0.0341(8) Uani 1 1 d . . . . .
O5 O 1.0327(4) 0.7776(3) 0.6057(4) 0.0377(9) Uani 1 1 d G . . . .
H5A H 0.971166 0.810551 0.652713 0.057 Uiso 1 1 d G U . . .
H5B H 1.105744 0.818429 0.596008 0.057 Uiso 1 1 d G U . . .
N8 N 0.4975(4) 0.9312(2) 0.3398(3) 0.0178(7) Uani 1 1 d . . . . .
N3 N 0.6903(4) 0.6573(2) 0.4933(3) 0.0191(7) Uani 1 1 d . . . . .
N4 N 0.5488(4) 0.7760(3) 0.5932(3) 0.0233(8) Uani 1 1 d . . . . .
H4A H 0.520923 0.731047 0.650159 0.028 Uiso 1 1 calc R U . . .
H4B H 0.515753 0.837367 0.598035 0.028 Uiso 1 1 calc R U . . .
N2 N 0.6512(4) 0.5787(3) 0.5703(4) 0.0226(8) Uani 1 1 d . . . . .
N1 N 0.8157(4) 0.5307(3) 0.4159(4) 0.0220(7) Uani 1 1 d . . . . .
N7 N 0.7293(4) 0.9957(3) 0.4272(3) 0.0201(7) Uani 1 1 d . . . . .
N6 N 0.8401(4) 0.6901(3) 0.3106(4) 0.0241(8) Uani 1 1 d . . . . .
N5 N 0.7885(4) 0.7835(3) 0.3132(3) 0.0223(8) Uani 1 1 d . . . . .
N9 N 1.1064(5) 0.6149(3) 0.7867(4) 0.0324(10) Uani 1 1 d G . . . .
H9A H 1.083393 0.664863 0.735455 0.049 Uiso 1 1 d DG U . . .
H9B H 1.192207 0.630344 0.821672 0.049 Uiso 1 1 d DG U . . .
C6 C 0.6385(4) 0.9170(3) 0.3896(4) 0.0187(8) Uani 1 1 d . . . . .
C5 C 0.6943(4) 0.8149(3) 0.4011(4) 0.0183(8) Uani 1 1 d . . . . .
C3 C 0.6386(4) 0.7518(3) 0.5018(4) 0.0176(8) Uani 1 1 d . . . . .
C4 C 0.7880(4) 0.6280(3) 0.3999(4) 0.0205(8) Uani 1 1 d . . . . .
C2 C 0.7303(4) 0.5074(3) 0.5174(4) 0.0206(8) Uani 1 1 d . . . . .
C1 C 0.7275(5) 0.4035(3) 0.5713(5) 0.0261(7) Uani 1 1 d D . . . .
F1A F 0.8485(12) 0.3770(11) 0.6396(10) 0.0327(16) Uani 0.5 1 d D . P A 2
F3A F 0.5995(15) 0.3917(19) 0.632(3) 0.0278(16) Uani 0.5 1 d D . P A 2
F2A F 0.7495(17) 0.3325(12) 0.4848(15) 0.0333(18) Uani 0.5 1 d D . P A 2
H9C H 1.125(5) 0.566(2) 0.732(4) 0.058(19) Uiso 1 1 d D . . . .
H9D H 1.050(4) 0.601(3) 0.848(6) 0.06(2) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F3 C1 1.319(10) . ?
O2 N8 1.238(4) . ?
O1 N8 1.274(4) . ?
F2 C1 1.368(9) . ?
O3 N7 1.246(4) . ?
F1 C1 1.371(9) . ?
O4 N7 1.260(4) . ?
O5 H5A 0.8698 . ?
O5 H5B 0.8699 . ?
N8 C6 1.374(5) . ?
N3 N2 1.369(5) . ?
N3 C3 1.359(5) . ?
N3 C4 1.380(5) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N4 C3 1.298(5) . ?
N2 C2 1.324(5) . ?
N1 C4 1.341(5) . ?
N1 C2 1.349(6) . ?
N7 C6 1.386(5) . ?
N6 N5 1.341(5) . ?
N6 C4 1.331(5) . ?
N5 C5 1.328(5) . ?
N9 H9A 0.8700 . ?
N9 H9B 0.8700 . ?
N9 H9C 0.88(3) . ?
N9 H9D 0.84(5) . ?
C6 C5 1.467(6) . ?
C5 C3 1.434(6) . ?
C2 C1 1.500(6) . ?
C1 F1A 1.327(9) . ?
C1 F3A 1.347(10) . ?
C1 F2A 1.316(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H5A O5 H5B 104.5 . . ?
O2 N8 O1 120.6(3) . . ?
O2 N8 C6 124.1(3) . . ?
O1 N8 C6 115.2(3) . . ?
N2 N3 C4 111.0(3) . . ?
C3 N3 N2 126.0(3) . . ?
C3 N3 C4 123.0(4) . . ?
H4A N4 H4B 120.0 . . ?
C3 N4 H4A 120.0 . . ?
C3 N4 H4B 120.0 . . ?
C2 N2 N3 99.9(3) . . ?
C4 N1 C2 102.0(3) . . ?
O3 N7 O4 120.6(3) . . ?
O3 N7 C6 123.6(3) . . ?
O4 N7 C6 115.8(3) . . ?
C4 N6 N5 116.2(3) . . ?
C5 N5 N6 123.0(4) . . ?
H9A N9 H9B 104.5 . . ?
H9A N9 H9C 104.5 . . ?
H9A N9 H9D 117.8 . . ?
H9B N9 H9C 104.4 . . ?
H9B N9 H9D 108.2 . . ?
H9C N9 H9D 116(3) . . ?
N8 C6 N7 122.2(3) . . ?
N8 C6 C5 118.3(3) . . ?
N7 C6 C5 119.5(3) . . ?
N5 C5 C6 118.3(4) . . ?
N5 C5 C3 123.0(4) . . ?
C3 C5 C6 118.7(4) . . ?
N3 C3 C5 112.0(4) . . ?
N4 C3 N3 120.5(4) . . ?
N4 C3 C5 127.4(4) . . ?
N1 C4 N3 108.6(4) . . ?
N6 C4 N3 122.7(4) . . ?
N6 C4 N1 128.7(4) . . ?
N2 C2 N1 118.5(4) . . ?
N2 C2 C1 120.7(4) . . ?
N1 C2 C1 120.8(4) . . ?
F3 C1 F2 103.7(19) . . ?
F3 C1 F1 97.8(14) . . ?
F3 C1 C2 116.9(10) . . ?
F2 C1 F1 124.7(8) . . ?
F2 C1 C2 107.4(9) . . ?
F1 C1 C2 106.9(8) . . ?
F1A C1 C2 114.5(8) . . ?
F1A C1 F3A 116.3(13) . . ?
F3A C1 C2 107.7(10) . . ?
F2A C1 C2 115.4(10) . . ?
F2A C1 F1A 90.5(8) . . ?
F2A C1 F3A 112.0(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 N8 C6 N7 -5.3(6) . . . . ?
O2 N8 C6 C5 175.6(4) . . . . ?
O1 N8 C6 N7 176.5(3) . . . . ?
O1 N8 C6 C5 -2.6(5) . . . . ?
O3 N7 C6 N8 3.3(6) . . . . ?
O3 N7 C6 C5 -177.6(4) . . . . ?
O4 N7 C6 N8 -177.5(4) . . . . ?
O4 N7 C6 C5 1.6(6) . . . . ?
N8 C6 C5 N5 104.2(5) . . . . ?
N8 C6 C5 C3 -72.4(5) . . . . ?
N3 N2 C2 N1 0.1(5) . . . . ?
N3 N2 C2 C1 178.7(4) . . . . ?
N2 N3 C3 N4 3.5(6) . . . . ?
N2 N3 C3 C5 -176.1(4) . . . . ?
N2 N3 C4 N1 -1.0(5) . . . . ?
N2 N3 C4 N6 178.3(4) . . . . ?
N2 C2 C1 F3 19.7(16) . . . . ?
N2 C2 C1 F2 135.6(8) . . . . ?
N2 C2 C1 F1 -88.5(6) . . . . ?
N2 C2 C1 F1A -106.6(6) . . . . ?
N2 C2 C1 F3A 24.4(15) . . . . ?
N2 C2 C1 F2A 150.3(8) . . . . ?
N1 C2 C1 F3 -161.7(15) . . . . ?
N1 C2 C1 F2 -45.8(9) . . . . ?
N1 C2 C1 F1 90.1(7) . . . . ?
N1 C2 C1 F1A 72.0(7) . . . . ?
N1 C2 C1 F3A -157.0(14) . . . . ?
N1 C2 C1 F2A -31.1(9) . . . . ?
N7 C6 C5 N5 -74.9(5) . . . . ?
N7 C6 C5 C3 108.5(4) . . . . ?
N6 N5 C5 C6 -176.4(4) . . . . ?
N6 N5 C5 C3 0.0(6) . . . . ?
N5 N6 C4 N3 -2.1(6) . . . . ?
N5 N6 C4 N1 177.0(4) . . . . ?
N5 C5 C3 N3 -1.8(6) . . . . ?
N5 C5 C3 N4 178.6(4) . . . . ?
C6 C5 C3 N3 174.7(3) . . . . ?
C6 C5 C3 N4 -4.9(6) . . . . ?
C3 N3 N2 C2 178.5(4) . . . . ?
C3 N3 C4 N1 -179.0(4) . . . . ?
C3 N3 C4 N6 0.3(6) . . . . ?
C4 N3 N2 C2 0.5(4) . . . . ?
C4 N3 C3 N4 -178.8(4) . . . . ?
C4 N3 C3 C5 1.6(5) . . . . ?
C4 N1 C2 N2 -0.7(5) . . . . ?
C4 N1 C2 C1 -179.3(4) . . . . ?
C4 N6 N5 C5 1.9(6) . . . . ?
C2 N1 C4 N3 0.9(4) . . . . ?
C2 N1 C4 N6 -178.3(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
